Dicyclohexylcarbodiimide → 2,5-dioxopyrrolidin-1-yl(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

HRID 2386110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2386110
[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:7]([NH:9][C@H:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])([O-:3])=[O:2].O[N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([N+:24]([O-:26])=[O:25])[CH:23]=1)[C:7]([NH:9][C@H:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][C:12]([O:14][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])=[O:13])=[O:8])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 44255973(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid

Produkt 1

HCID 866343152,5-dioxopyrrolidin-1-yl(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

12 g of (S)-3-(3,5-dinitrobenzamido)-3-phenylpropionic acid from reaction b) were dissolved in 120 ml of tetrahydrofuran and admixed with 3.92 g of N-hydroxysuccinimide. With cooling in an icebath at 0-5° C., 7.1 g of dicyclohexylcarbodiimide was added in portions to the reaction mixture. On completion of addition, the mixture was left in the icebath with further stirring until the solution reached room temperature. After the reaction ended (HPLC monitoring >95 area % conversion), the precipitated dicyclohexylurea was filtered off and washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure, and the residue digested at reflux in 250 ml of 2-propanol for 2 h. The product was filtered off with suction, washed with 2-propanol and dried at 50° C. under reduced pressure. The yield was 13.87 g; HPLC purity 98.8 area %.

Aufarbeitung

  1. additionOn completion of addition
  2. waitthe mixture was left in the icebath
  3. customreached room temperature
  4. filtrationthe precipitated dicyclohexylurea was filtered off
  5. washwashed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. temperatureat reflux in 250 ml of 2-propanol for 2 h
  8. filtrationThe product was filtered off with suction
  9. washwashed with 2-propanol
  10. customdried at 50° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-513f8e9e8558458d9d1298c885faa10f
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268631B2

Notizen zur Reaktion

Wird geladen…